1-ethyl-6-fluoro-4-oxo-7-(4-[4-fluorobenzoylhydrazonomethyl]piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid | 1340587-10-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-ethyl-6-fluoro-4-oxo-7-(4-[4-fluorobenzoylhydrazonomethyl]piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid
• 英文别名: 1-ethyl-6-fluoro-7-[4-[[(4-fluorobenzoyl)hydrazinylidene]methyl]piperazin-1-yl]-4-oxoquinoline-3-carboxylic acid
• CAS: 1340587-10-1
• 化学式: C₂₄H₂₃F₂N₅O₄
• 分子量: 483.475
• InChiKey: MJPZXACRRBQEGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.49
• 重原子数：
  35.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  107.24
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  、 诺氟沙星 在 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 5.67h， 以44%的产率得到1-ethyl-6-fluoro-4-oxo-7-(4-[4-fluorobenzoylhydrazonomethyl]piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  New fluorine-containing hydrazones active against MDR-tuberculosis

  摘要：

  Several new fluorine-containing hydrazones were synthesized and screened for their in vitro anti-mycobacterial activity. Nine of these derivatives have shown a remarkable activity against MDR-TB strain with MIC 0.5 mu g/mL and high value of selectivity index (SI). Compound 3h with the highest SI (1268.58) was used for stability evaluation with putative metabolites (ciprofloxacin and formylciprofloxacin) detection. Compound 3h was stable at pH 7.4 of aqueous buffer and rat plasma, in acidic buffers (at pH 3 and 5) slow decomposition was observed. Interestingly, no formylciprofloxacin was detected in the solution, and only slightly increased concentration of ciprofloxacin was observed instead. Trifluoromethyl hydrazones 3f and 3g exhibited the best activity also against two strains of Mycobacterium kansasii (MIC 1-4 mu mol/L). All evaluated compounds were found to be non-cytotoxic. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.07.052

文献信息

• New fluorine-containing hydrazones active against MDR-tuberculosis
  作者：Eva Vavříková、Slovenko Polanc、Marijan Kočevar、Kata Horváti、Szilvia Bősze、Jiřina Stolaříková、Kateřina Vávrová、Jarmila Vinšová

  DOI：10.1016/j.ejmech.2011.07.052

  日期：2011.10

  Several new fluorine-containing hydrazones were synthesized and screened for their in vitro anti-mycobacterial activity. Nine of these derivatives have shown a remarkable activity against MDR-TB strain with MIC 0.5 mu g/mL and high value of selectivity index (SI). Compound 3h with the highest SI (1268.58) was used for stability evaluation with putative metabolites (ciprofloxacin and formylciprofloxacin) detection. Compound 3h was stable at pH 7.4 of aqueous buffer and rat plasma, in acidic buffers (at pH 3 and 5) slow decomposition was observed. Interestingly, no formylciprofloxacin was detected in the solution, and only slightly increased concentration of ciprofloxacin was observed instead. Trifluoromethyl hydrazones 3f and 3g exhibited the best activity also against two strains of Mycobacterium kansasii (MIC 1-4 mu mol/L). All evaluated compounds were found to be non-cytotoxic. (C) 2011 Elsevier Masson SAS. All rights reserved.